JP2006348278A - カルボキシル基含有ポリウレタン、熱硬化性樹脂組成物およびそれらの用途 - Google Patents
カルボキシル基含有ポリウレタン、熱硬化性樹脂組成物およびそれらの用途 Download PDFInfo
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- JP2006348278A JP2006348278A JP2006136826A JP2006136826A JP2006348278A JP 2006348278 A JP2006348278 A JP 2006348278A JP 2006136826 A JP2006136826 A JP 2006136826A JP 2006136826 A JP2006136826 A JP 2006136826A JP 2006348278 A JP2006348278 A JP 2006348278A
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- Prior art keywords
- carboxyl group
- polyol
- containing polyurethane
- mol
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 title claims abstract description 141
- 229920002635 polyurethane Polymers 0.000 title claims abstract description 116
- 239000004814 polyurethane Substances 0.000 title claims abstract description 116
- 229920001187 thermosetting polymer Polymers 0.000 title claims description 45
- 239000011342 resin composition Substances 0.000 title claims description 44
- 150000003077 polyols Chemical class 0.000 claims abstract description 130
- 229920005862 polyol Polymers 0.000 claims abstract description 120
- 229920002857 polybutadiene Polymers 0.000 claims abstract description 52
- 239000005062 Polybutadiene Substances 0.000 claims abstract description 51
- 239000002994 raw material Substances 0.000 claims abstract description 31
- 229920001195 polyisoprene Polymers 0.000 claims abstract description 23
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 20
- 239000000463 material Substances 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims description 84
- 229920000647 polyepoxide Polymers 0.000 claims description 60
- 239000003822 epoxy resin Substances 0.000 claims description 54
- 239000002904 solvent Substances 0.000 claims description 48
- 239000005056 polyisocyanate Substances 0.000 claims description 39
- 229920001228 polyisocyanate Polymers 0.000 claims description 39
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 claims description 38
- 239000002253 acid Substances 0.000 claims description 36
- 229910000679 solder Inorganic materials 0.000 claims description 34
- 239000007787 solid Substances 0.000 claims description 24
- -1 nitrogen-containing heterocyclic compounds Chemical class 0.000 claims description 20
- JVYDLYGCSIHCMR-UHFFFAOYSA-N 2,2-bis(hydroxymethyl)butanoic acid Chemical compound CCC(CO)(CO)C(O)=O JVYDLYGCSIHCMR-UHFFFAOYSA-N 0.000 claims description 19
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 claims description 19
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims description 19
- 239000003795 chemical substances by application Substances 0.000 claims description 17
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims description 14
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 claims description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 13
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 11
- XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 10
- 239000010419 fine particle Substances 0.000 claims description 10
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 claims description 8
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 8
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 claims description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 8
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 8
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- 150000001412 amines Chemical class 0.000 claims description 7
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 6
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 claims description 6
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 6
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 claims description 6
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 claims description 6
- MLFHJEHSLIIPHL-UHFFFAOYSA-N isoamyl acetate Chemical compound CC(C)CCOC(C)=O MLFHJEHSLIIPHL-UHFFFAOYSA-N 0.000 claims description 6
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims description 6
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 claims description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 6
- LIPRQQHINVWJCH-UHFFFAOYSA-N 1-ethoxypropan-2-yl acetate Chemical compound CCOCC(C)OC(C)=O LIPRQQHINVWJCH-UHFFFAOYSA-N 0.000 claims description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 5
- 150000001334 alicyclic compounds Chemical class 0.000 claims description 5
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 claims description 4
- LAVARTIQQDZFNT-UHFFFAOYSA-N 1-(1-methoxypropan-2-yloxy)propan-2-yl acetate Chemical compound COCC(C)OCC(C)OC(C)=O LAVARTIQQDZFNT-UHFFFAOYSA-N 0.000 claims description 4
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 claims description 4
- RDFQSFOGKVZWKF-UHFFFAOYSA-N 3-hydroxy-2,2-dimethylpropanoic acid Chemical compound OCC(C)(C)C(O)=O RDFQSFOGKVZWKF-UHFFFAOYSA-N 0.000 claims description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000004305 biphenyl Substances 0.000 claims description 4
- 235000010290 biphenyl Nutrition 0.000 claims description 4
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 claims description 4
- 125000003700 epoxy group Chemical group 0.000 claims description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 claims description 4
- 239000002798 polar solvent Substances 0.000 claims description 4
- 239000008096 xylene Substances 0.000 claims description 4
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 claims description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 3
- 150000007514 bases Chemical class 0.000 claims description 3
- 238000009835 boiling Methods 0.000 claims description 3
- UHKJHMOIRYZSTH-UHFFFAOYSA-N ethyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OCC UHKJHMOIRYZSTH-UHFFFAOYSA-N 0.000 claims description 3
- WHRLOJCOIKOQGL-UHFFFAOYSA-N ethyl 2-methoxypropanoate Chemical compound CCOC(=O)C(C)OC WHRLOJCOIKOQGL-UHFFFAOYSA-N 0.000 claims description 3
- 229940116333 ethyl lactate Drugs 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 150000004678 hydrides Chemical class 0.000 claims description 3
- 229940117955 isoamyl acetate Drugs 0.000 claims description 3
- YVWPDYFVVMNWDT-UHFFFAOYSA-N methyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OC YVWPDYFVVMNWDT-UHFFFAOYSA-N 0.000 claims description 3
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 claims description 3
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 2
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- 150000008065 acid anhydrides Chemical class 0.000 claims description 2
- 229930188620 butyrolactone Natural products 0.000 claims description 2
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- DVQHRBFGRZHMSR-UHFFFAOYSA-N sodium methyl 2,2-dimethyl-4,6-dioxo-5-(N-prop-2-enoxy-C-propylcarbonimidoyl)cyclohexane-1-carboxylate Chemical compound [Na+].C=CCON=C(CCC)[C-]1C(=O)CC(C)(C)C(C(=O)OC)C1=O DVQHRBFGRZHMSR-UHFFFAOYSA-N 0.000 description 15
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- QEXITCCVENILJI-UHFFFAOYSA-M tributyl(phenyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)C1=CC=CC=C1 QEXITCCVENILJI-UHFFFAOYSA-M 0.000 description 1
- GLSQMJPVEVGXMZ-UHFFFAOYSA-N tributyl-(2,5-dihydroxyphenyl)phosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)C1=CC(O)=CC=C1O GLSQMJPVEVGXMZ-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- YFNKIDBQEZZDLK-UHFFFAOYSA-N triglyme Chemical compound COCCOCCOCCOC YFNKIDBQEZZDLK-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- RUDFQVOCFDJEEF-UHFFFAOYSA-N yttrium(III) oxide Inorganic materials [O-2].[O-2].[O-2].[Y+3].[Y+3] RUDFQVOCFDJEEF-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Polyurethanes Or Polyureas (AREA)
- Epoxy Resins (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2007125806A1 (ja) * | 2006-04-28 | 2007-11-08 | Showa Denko K.K. | 熱硬化性樹脂組成物およびその用途 |
| WO2009057497A1 (ja) * | 2007-11-01 | 2009-05-07 | Kuraray Co., Ltd. | ポリウレタン組成物 |
| WO2009116609A1 (ja) * | 2008-03-21 | 2009-09-24 | 昭和電工株式会社 | 樹脂組成物及びその硬化膜 |
| JP2009280686A (ja) * | 2008-05-21 | 2009-12-03 | Hitachi Chem Co Ltd | 熱硬化性樹脂組成物 |
| WO2010084871A1 (ja) | 2009-01-20 | 2010-07-29 | 昭和電工株式会社 | カルボキシル基含有ポリウレタン |
| WO2010084872A1 (ja) | 2009-01-20 | 2010-07-29 | 昭和電工株式会社 | （ポリ）カーボネートポリオールおよび該（ポリ）カーボネートポリオールを原料とするカルボキシル基含有ポリウレタン |
| US8999220B2 (en) | 2007-10-19 | 2015-04-07 | Showa Denko K.K. | Method and apparatus for manufacturing resin stamper, imprint method, magnetic recording medium, and magnetic recording/reproducing apparatus |
| WO2017110326A1 (ja) | 2015-12-25 | 2017-06-29 | 昭和電工株式会社 | 硬化性組成物、硬化物、オーバーコート膜、被覆フレキシブル配線板およびその製造方法 |
| KR20180073611A (ko) | 2015-12-25 | 2018-07-02 | 쇼와 덴코 가부시키가이샤 | 신규 폴리우레탄, 경화성 조성물, 오버코트막, 플렉시블 배선판 및 그 제조 방법 |
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| JPH08208783A (ja) * | 1994-10-27 | 1996-08-13 | Hoechst Ag | 不飽和ポリウレタンを基本成分とする反応性乳化剤 |
| JP2001342232A (ja) * | 2000-03-30 | 2001-12-11 | Sanyo Chem Ind Ltd | 活性光線硬化性組成物 |
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| JPH08208783A (ja) * | 1994-10-27 | 1996-08-13 | Hoechst Ag | 不飽和ポリウレタンを基本成分とする反応性乳化剤 |
| JP2001342232A (ja) * | 2000-03-30 | 2001-12-11 | Sanyo Chem Ind Ltd | 活性光線硬化性組成物 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2007125806A1 (ja) * | 2006-04-28 | 2007-11-08 | Showa Denko K.K. | 熱硬化性樹脂組成物およびその用途 |
| US8999220B2 (en) | 2007-10-19 | 2015-04-07 | Showa Denko K.K. | Method and apparatus for manufacturing resin stamper, imprint method, magnetic recording medium, and magnetic recording/reproducing apparatus |
| WO2009057497A1 (ja) * | 2007-11-01 | 2009-05-07 | Kuraray Co., Ltd. | ポリウレタン組成物 |
| TWI458772B (zh) * | 2008-03-21 | 2014-11-01 | 昭和電工股份有限公司 | Resin composition and hardened film thereof |
| WO2009116609A1 (ja) * | 2008-03-21 | 2009-09-24 | 昭和電工株式会社 | 樹脂組成物及びその硬化膜 |
| KR101631540B1 (ko) | 2008-03-21 | 2016-06-17 | 쇼와 덴코 가부시키가이샤 | 수지 조성물 및 그 경화막 |
| KR20100133358A (ko) * | 2008-03-21 | 2010-12-21 | 쇼와 덴코 가부시키가이샤 | 수지 조성물 및 그 경화막 |
| JPWO2009116609A1 (ja) * | 2008-03-21 | 2011-07-21 | 昭和電工株式会社 | 樹脂組成物及びその硬化膜 |
| JP2009280686A (ja) * | 2008-05-21 | 2009-12-03 | Hitachi Chem Co Ltd | 熱硬化性樹脂組成物 |
| US8674017B2 (en) | 2009-01-20 | 2014-03-18 | Showa Denko K.K. | (Poly)carbonate polyol and carboxyl group-containing polyurethane obtained from the (poly)carbonate polyol |
| WO2010084872A1 (ja) | 2009-01-20 | 2010-07-29 | 昭和電工株式会社 | （ポリ）カーボネートポリオールおよび該（ポリ）カーボネートポリオールを原料とするカルボキシル基含有ポリウレタン |
| WO2010084871A1 (ja) | 2009-01-20 | 2010-07-29 | 昭和電工株式会社 | カルボキシル基含有ポリウレタン |
| WO2017110326A1 (ja) | 2015-12-25 | 2017-06-29 | 昭和電工株式会社 | 硬化性組成物、硬化物、オーバーコート膜、被覆フレキシブル配線板およびその製造方法 |
| KR20180066194A (ko) | 2015-12-25 | 2018-06-18 | 쇼와 덴코 가부시키가이샤 | 경화성 조성물, 경화물, 오버코트막, 피복 플렉시블 배선판 및 그 제조 방법 |
| KR20180073611A (ko) | 2015-12-25 | 2018-07-02 | 쇼와 덴코 가부시키가이샤 | 신규 폴리우레탄, 경화성 조성물, 오버코트막, 플렉시블 배선판 및 그 제조 방법 |
| US10889729B2 (en) | 2015-12-25 | 2021-01-12 | Nippon Polytech Corp. | Curable composition, cured object, overcoat film, coated flexible wiring board, and process for producing same |
| US11044807B2 (en) | 2015-12-25 | 2021-06-22 | Nippon Polytech Corp. | Polyurethane, curable composition, overcoat film, and flexible wiring board and production method therefor |
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